Enantio-selective preparation of (S)-1-phenylethanol by a novel marine GDSL lipase MT6 with reverse stereo-selectivity

doi:10.1016/S1872-2067(16)62505-6

Chinese Journal of Catalysis ›› 2016, Vol. 37 ›› Issue (11): 1966-1974.DOI: 10.1016/S1872-2067(16)62505-6

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Enantio-selective preparation of (S)-1-phenylethanol by a novel marine GDSL lipase MT6 with reverse stereo-selectivity

Dun Deng^a,b,c, Yun Zhang^a,b, Aijun Sun^a,b, Yunfeng Hu^a,b,d

a Key Laboratory of Tropical Marine Bio-resources and Ecology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, Guangdong, China;
b Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, Guangzhou 510301, Guangdong, China;
c Institute of Animal Science, Guangdong Academy of Agricultural Science, Guangzhou 510640, Guangdong, China;
d South China Sea Bio-Resource Exploitation and Utilization Collaborative Innovation Center, Guangzhou 510275, Guangdong, China

Received:2016-05-31 Revised:2016-07-13 Online:2016-11-25 Published:2016-11-25
Contact: Yunfeng Hu,Tel:+86-20-89024092; Fax:+86-20-84451672; E-mail:yunfeng.hu@scsio.ac.cn
Supported by:
This work was supported by the Strategic Priority Research Program of Chinese Academy of Sciences (XDA11030404), the National Natural Science Foundation of China (21302199), Guangzhou Science and Technology Plan Projects (201510010012), and the Key Project from Chinese Academy of Sciences (KGZD-EW-606).

Abstract

Abstract:

We previously functionally characterized a novel marine microbial GDSL lipase MT6 and identified that the stereo-selectivity of MT6 was opposite to that of other common lipases in trans-esterification reactions. Herein, we have investigated the use of MT6 in stereo-selective bio-catalysis through direct hydrolysis reactions. Notably, the stereo-selectivity of MT6 was also demonstrated to be opposite to that of other common lipases in hydrolysis reactions. Parameters, including temperature, organic co-solvents, pH, ionic strength, catalyst loading, substrate concen-tration, and reaction time, affecting the enzymatic resolution of racemic 1-phenylethyl acetate were further investigated, with the e.e. of the final (S)-1-Phenylethanol product and the conversion being 97% and 28.5%, respectively, after process optimization. The lengths of side chains of 1-phenylethyl esters greatly affected the stereo-selectivity and conversion during kinetic resolutions. MT6 is a novel marine microbial GDSL lipase exhibiting opposite stereo-selectivities than other common lipases in both trans-esterification reactions and hydrolysis reactions.

Key words: GDSL lipase, Biocatalysis, Kinetic resolution, Direct hydrolysis, (S)-1-Phenylethanol, Reverse stereo-selectivity

Dun Deng, Yun Zhang, Aijun Sun, Yunfeng Hu. Enantio-selective preparation of (S)-1-phenylethanol by a novel marine GDSL lipase MT6 with reverse stereo-selectivity[J]. Chinese Journal of Catalysis, 2016, 37(11): 1966-1974.

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Enantio-selective preparation of (S)-1-phenylethanol by a novel marine GDSL lipase MT6 with reverse stereo-selectivity

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